CN1224716A - Method for synthesizing hymexazole technical product - Google Patents
Method for synthesizing hymexazole technical product Download PDFInfo
- Publication number
- CN1224716A CN1224716A CN 98100081 CN98100081A CN1224716A CN 1224716 A CN1224716 A CN 1224716A CN 98100081 CN98100081 CN 98100081 CN 98100081 A CN98100081 A CN 98100081A CN 1224716 A CN1224716 A CN 1224716A
- Authority
- CN
- China
- Prior art keywords
- reaction
- amination
- compound
- temperature
- acidylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title abstract description 6
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 52
- 238000005576 amination reaction Methods 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 22
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims abstract description 20
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000007112 amidation reaction Methods 0.000 claims abstract description 12
- 238000005917 acylation reaction Methods 0.000 claims abstract description 11
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000029936 alkylation Effects 0.000 claims abstract description 4
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 230000035484 reaction time Effects 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 22
- 230000009471 action Effects 0.000 claims description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 229940059260 amidate Drugs 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 claims description 15
- 238000010189 synthetic method Methods 0.000 claims description 11
- 150000002460 imidazoles Chemical class 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 230000009435 amidation Effects 0.000 claims description 9
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 7
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000007039 two-step reaction Methods 0.000 claims description 6
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract description 5
- 201000010099 disease Diseases 0.000 abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
- 238000003860 storage Methods 0.000 abstract description 2
- 230000010933 acylation Effects 0.000 abstract 3
- 239000005794 Hymexazol Substances 0.000 abstract 1
- 240000007594 Oryza sativa Species 0.000 abstract 1
- 235000007164 Oryza sativa Nutrition 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 235000013399 edible fruits Nutrition 0.000 abstract 1
- 235000009566 rice Nutrition 0.000 abstract 1
- 235000013311 vegetables Nutrition 0.000 abstract 1
- 238000004458 analytical method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- -1 compounds imidazoles Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a method for synthesizing hymexazole technical, which comprises the steps of taking trichlorotriphenol as a raw material, and carrying out alkylation, amination, acylation and amidation reactions with 1, 2-dibromoethane, propylamine, phosgene and imidazole step by step. In order to solve the problems of high product cost, long reaction period and low reaction yield, the amination, acylation and amidation reactions are carried out by using the same solvent, and the acylation and amidation reactions are continuously carried out in the same reactor. The hymexazol crude drug prepared by the method is mainly used for preventing and treating the growth and storage diseases of fruits, vegetables and rice.
Description
The present invention is a kind of synthetic method of hymexazole, relates to the preparation method of heterogeneous ring compound, and the hymexazole of this method preparation is mainly used in the control of fruit and vegetable and paddy growth and storage disease.
Hymexazole is the effective ingredient in the sterilant hymexazole missible oil, chemical name: 1-[N-2-(2,4, the 6-Trichlorophenoxy) ethyl-N-propyl group formamyl] imidazoles, popular name: Prochloraz.This series of compounds imidazoles sterilant, its action principle are to suppress biosynthetic process in the thalline, and the ascomycetes and the imperfect fungi disease of various crop had significant preventive effect, and be especially more effective when several diseases take place simultaneously.United States Patent (USP) 3; 991; 071 has reported " bacteriocide formula that contains substituted imidazole compound "; synthetic method comprising above-mentioned hymexazole; this synthetic route comprises alkylation; amination; acidylate and amidate action; synthetic route is reasonable; starting material are cheap, but amination in the four-step reaction; absolute ethanol has been selected in acidylate and acid amides reaction respectively for use; ethyl acetate; tetrahydrofuran (THF) is as reaction solvent, these solvent price height; thereby improved cost; and the drying treatment difficulty, especially selected different solvents for use, per step reaction must separate except that neat solvent; separation and purification repeatedly and productive rate is reduced, and hindered carrying out continuously of reaction.More seriously chemical action can take place in reactant propylamine and solvent absolute ethanol, produces by product, in order to suppress the generation of side reaction, carries out at ambient temperature and limited temperature of reaction, and the reaction times reaches 7 days, makes reaction time long.
Purpose of the present invention is exactly in order to overcome disadvantages of background technology, designs the synthetic method of the hymexazole that a kind of cost is low, reaction time short, the reaction yield is high.
Design of the present invention: in order to realize above-mentioned purpose, select for use a kind of price low,, and three-step reaction is used with a kind of solvent, improve temperature of reaction, shorten reaction time, and acidylate with the amidation two-step reaction and carry out continuously not with the solvent of reactant effect.
The synthetic method of hymexazole of the present invention: the synthetic route and the reaction formula of this compound are as follows:
Comprising being raw material with the chemical compounds I, substep is with 1,2 one ethylene dibromides, propylamine, phosgene and imidazoles carry out alkylation, amination, acidylate and amidate action, be characterized in that amination, acidylate and amidate action use with a kind of solvent: 1,2-ethylene dichloride, toluene, chlorobenzene, hexanaphthene or benzene; Acidylate and acid amides two-step reaction carry out continuously; Amination reaction: compound ii is 1: 2～6mol with propylamine material ratio, 40～75 ℃ of temperature of reaction, reaction times 6～12h; Acylation reaction: the compound III is 1: 1～3mol with phosgene material ratio, 15～50 ℃ of temperature of reaction, reaction times 1～4h; Acid amides compound of reaction IV with imidazoles material ratio is: 1: 1～4mol, and 60～85 ℃ of temperature of reaction, reaction times 4～10h.
A kind of preferable reaction conditions of the present invention: amination, acidylate and amidate action select for use ethylene dichloride as solvent, and acidylate and amidation two-step reaction carry out in same reactor continuously; Amination reaction: compound ii is 1 with propylamine material ratio: 3mol, 55 ℃ of temperature of reaction, reaction times 8h; Acylation reaction: the compound III with phosgene material ratio is: 1: 1mol, 30 ℃ of temperature of reaction, reaction times 2h; Amidate action: the compound IV with imidazoles material ratio is: 1: 2mol, 80 ℃ of temperature of reaction, reaction times 6h.
The reaction conditions that another kind of the present invention is preferable: amination, acidylate and amidate action select for use toluene as solvent, and acidylate and amidation two-step reaction carry out in two reactors that pipeline is communicated with continuously; Amination reaction: compound ii with propylamine material ratio is: 1: 2mol, 45 ℃ of temperature of reaction, reaction times 10h; Acylation reaction: the compound III is 1 with phosgene material ratio: 1.5mol, 10 ℃ of temperature of reaction, reaction times 4h; Amidate action: the compound IV with imidazoles material ratio is: 1: 1.5mol, 70 ℃ of temperature of reaction, reaction times 8h.
Advantage of the present invention is as follows: 1. three-step reaction adopts single cheap solvent, has reduced production cost, has simplified separation, drying and has removed operation such as neat solvent.2. reactant and solvent do not have side reaction, thereby improve temperature of reaction and shortened reaction time, and reduce by product, improve degree of purity of production.3. the reaction of two steps is carried out continuously, has simplified operation, has improved productive rate.
Embodiment: 1. the synthetic method 1.1 of hymexazole of the present invention prepares β-bromo-2,4,6-trichlorobenzene ether (II) with reference to following reaction formula
In the 2000mol four-hole bottle of agitator, thermometer, prolong and feed hopper is housed, add chemical compounds I 376g (1.9mol) and ethylene dibromide 447.4g (2.38mol) and 47.4ml water and be heated to boiling, the solution that 83.6gNaOH is dissolved in 400ml water drips in 1h, stops heating behind the reaction 8h.After the cooling of question response thing, tell layer oily matter, normal pressure boils off less water and excessive ethylene dibromide, obtains 153～155 ℃/4mmHg cut 3769 through underpressure distillation, productive rate 65%, 49～50 ℃ of fusing points (49～50 ℃ of literature values).
Ultimate analysis: measured value: C31.43% H1.92%
Theoretical value: C31.53% H1.97%1.2 prepares N-2 with reference to following reaction formula, and 4,6-Trichlorophenoxy ethyl propylamine (III)
In the 2000ml four-hole boiling flask of agitator, thermometer, prolong and feed hopper is housed, add 219g (3.7mol) Tri N-Propyl Amine and 600ml ethylene dichloride, the question response thing is heated to 55 ℃, drip 376g (1.235mol) compound ii then and be dissolved in the solution of 200ml ethylene dichloride, 40min drips off back constant temperature 8h.Boil off excessive Tri N-Propyl Amine again, after the Tri N-Propyl Amine Hydrogen bromide double salt of separating out filtered, the NaOH solution-treated filtrate with 5N washed the filtrate secondary again with water, after the adding Anhydrous potassium carbonate thorough drying, filtered, boiled off solvent and obtain yellow oil.160～162 ℃/4mmHg cut is got in underpressure distillation, obtains product 334.6g, productive rate 95.9%.
Boiling point: 160～162 ℃/4mmHg (112～114 ℃ of literature values/0.2mmHg)
Ultimate analysis: measured value: C46.8% H4.8% N5.1%
Theoretical value: C46.7% H4.6% N4.96%1.3 prepares N-propyl group-N-2,4,6 trichlorobenzene oxygen ethylamino formyl chlorides (IV) with reference to following reaction formula
In the pre-dry 5000ml four-hole bottle of agitator, thermometer, prolong and feed hopper is housed, add 334.6g (1.184mol) compound III and 3000ml ethylene dichloride, be heated to 30 ℃, drip 293g (2.96mol) phosgene and be dissolved in the 700ml ethylene dichloride, keep temperature of reaction to be no more than 40 ℃, after dropwising, stir 30min in 40 ℃ of continuation, then slowly heating up in the 30min reaches 50 ℃, and constant temperature 1h, feed dry air, remove remaining phosgene.1.4 with reference to following reaction formula preparation 1 (N-2-2,4,6-trichlorobenzene oxygen ethyl-N-propyl group amino
With 1.3 the constant temperature 1h reaction soln of removing phosgene add 161g (2.36mol) imidazoles, be heated to 80 ℃, behind the constant temperature 6h, cooling, filtration, filtrate water is given a baby a bath on the third day after its birth inferior, use the anhydrous magnesium sulfate thorough drying, elimination siccative, solvent distillation obtain yellow oil 398g, and the cooling back becomes white solid, productive rate 89.2%, purity 97.9%.1.5 it is as follows that the present invention prepares the finished product compound V analytical test result:
Be the prism-shaped shadow with the sherwood oil recrystallization, fusing point: 47.3～49.5 ℃ (44～46 ℃ of literature values)
Ultimate analysis: measured value: C47.79% H4.37% N11.45%
Theoretical value: C47.81% H4.25% N11.16%
Product through nucleus magnetic resonance, infrared, stratographic analysis and import is in full accord.
The compound V of hymexazole synthetic method of the present invention preparation is mixed with Shi Baoke 25% missible oil that German Ai Gefu company produces, and is the same with external product through preliminary trial effect, proves that this synthetic method is feasible.2. the present invention implements with reference to embodiment 1, and its implementation method and result are basic identical, and different reaction conditionss is that solvent is selected toluene for use, reacting material ratio (mol): amination 1: 2, acidylate 1: 1.5, amidation 1: 1.5; Temperature of reaction: 45 ℃ of aminations, 10 ℃ of acidylates, 70 ℃ of amidations; Reaction times: amination 10h, acidylate 4h, amidation 8h.The reaction of acidylate and acid amides uses the pipeline that has strainer to be communicated with two reactors in addition, after acylation reaction is finished, opens pipeline valve, and reaction soln separates with the throw out of reaction in another reactor, continues to finish amidate action.
3,4,5 embodiment implement with reference to embodiment 1, and its implementation method and result are basic identical, and different reaction conditionss are listed as follows:
| Embodiment | Reaction conditions | Amination reaction | Acylation reaction | The acid amides reaction |
| ????3 | Material is than (mol) | ????1∶5 | ????1∶2 | ????1∶4 |
| Temperature (℃) | ????60 | ????15 | ????65 | |
| Time (h) | ????6 | ????1 | ????5 | |
| Solvent | Chlorobenzene | |||
| ????4 | Material is than (mol) | ????1∶4 | ????1∶1.8 | ????1∶2 |
| Temperature (℃) | ????65 | ????40 | ????75 | |
| Time (h) | ????7 | ????3 | ????7 | |
| Solvent | Hexanaphthene | |||
| ????5 | Material is than (mol) | ????1∶6 | ????1∶3 | ????1∶4 |
| Temperature (℃) | ????70 | ????50 | ????80 | |
| Time (h) | ????12 | ????2 | ????9 | |
| Solvent | Benzene | |||
Claims (3)
1. the synthetic method of a hymexazole, the synthetic route and the reaction formula of this compound are as follows:
Comprising being raw material with the chemical compounds I, substep is with 1,2-ethylene dibromide, propylamine, phosgene and imidazoles carry out alkylation, amination, acidylate and amidate action, it is characterized in that amination, acidylate and amidate action select for use with a kind of solvent: 1,2-ethylene dichloride, toluene, chlorobenzene, hexanaphthene or benzene; Acidylate and amidation two-step reaction carry out continuously; Amination reaction: compound ii is 1: 2～6mol with propylamine material ratio, 40～75 ℃ of temperature of reaction, reaction times 6～12h; Acylation reaction: the compound III is 1: 1～3mol with phosgene material ratio, 15～50 ℃ of temperature of reaction, reaction times 1～4h; Amidate action: the compound IV with imidazoles material ratio is: 1: 1～4mol, and 60～85 ℃ of temperature of reaction, reaction times 4～10h.
2. synthetic method according to claim 1 is characterized in that preferable reaction conditions: amination, acidylate and amidate action select 1 for use, and the 2-ethylene dichloride is as solvent, and acidylate and amidation two-step reaction carry out in same reactor continuously; Amination reaction: compound ii is 1 with propylamine material ratio: 3mol, react 55 ℃, reaction times 8h; Acylation reaction: the compound III is 1: 1 with phosgene material ratio, 30 ℃ of temperature of reaction, reaction times 2h; Amidate action: the compound IV is 1 with imidazoles material ratio: 2mol, 80 ℃ of temperature of reaction, reaction times 6h.
3. synthetic method according to claim 1 is characterized in that preferable reaction conditions: amination, acidylate and amidate action select for use toluene as solvent, and two of acidylate and amidations are not reflected in two reactors that pipeline is communicated with to be carried out continuously; Amination reaction: compound ii is 1 with propylamine material ratio: 2mol, 45 ℃ of temperature of reaction, and reaction times 10h; Acylation reaction: the compound III is 1 with phosgene material ratio: 1.5mol, 10 ℃ of temperature of reaction, reaction times 4h; Amidate action: the compound IV is 1 with imidazoles material ratio: 1.5mol, 70 ℃ of temperature of reaction, reaction times 8h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 98100081 CN1224716A (en) | 1998-01-26 | 1998-01-26 | Method for synthesizing hymexazole technical product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 98100081 CN1224716A (en) | 1998-01-26 | 1998-01-26 | Method for synthesizing hymexazole technical product |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1224716A true CN1224716A (en) | 1999-08-04 |
Family
ID=5215794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 98100081 Pending CN1224716A (en) | 1998-01-26 | 1998-01-26 | Method for synthesizing hymexazole technical product |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1224716A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100340550C (en) * | 2005-09-16 | 2007-10-03 | 华南师范大学 | Method for preparing prochloraz |
| CN107011124A (en) * | 2017-03-15 | 2017-08-04 | 常州市天华制药有限公司 | A kind of production method of triphen phenolic compound |
| RU2789124C1 (en) * | 2022-02-25 | 2023-01-30 | Акционерное общество Фирма "Август" | Industrial method of obtaining prochlorase |
-
1998
- 1998-01-26 CN CN 98100081 patent/CN1224716A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100340550C (en) * | 2005-09-16 | 2007-10-03 | 华南师范大学 | Method for preparing prochloraz |
| CN107011124A (en) * | 2017-03-15 | 2017-08-04 | 常州市天华制药有限公司 | A kind of production method of triphen phenolic compound |
| CN107011124B (en) * | 2017-03-15 | 2020-12-01 | 常州市天华制药有限公司 | Production method of trisphenol compound |
| RU2789124C1 (en) * | 2022-02-25 | 2023-01-30 | Акционерное общество Фирма "Август" | Industrial method of obtaining prochlorase |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60013021T2 (en) | Preparation of S, S and R, S amino acid isosteres | |
| CN114573560A (en) | Preparation method of Voranolan fumarate | |
| CN1224716A (en) | Method for synthesizing hymexazole technical product | |
| CN109705048B (en) | Clean preparation method of tebuconazole | |
| CN102584681A (en) | Synthesis of high-purity mepiquat chloride serving as plant growth regulator with one-step method | |
| CN100427460C (en) | Method for synthesis of L-norvaline | |
| CN111269190A (en) | Method for synthesizing triazoline thioketone compound by one-pot method | |
| CN112479853B (en) | Preparation method of D-2-chloropropionyl chloride and D-2-chloropropionyl chloride | |
| CN107698471A (en) | It is a kind of to MSM benzaldehyde preparation method | |
| CN110003083B (en) | Process method for preparing S-indoline-2-carboxylic acid by using Ir catalyst | |
| CN112279805B (en) | Process for preparing 1- (3-methoxypyridin-2-yl) -2-propanone | |
| CN110498764B (en) | Synthesis method of doxylamine succinate | |
| CN102336766A (en) | Method for preparation of racemic clopidogrel via one-pot process | |
| CN110642722A (en) | Method for preparing N, N-tetramethyl decamethylene diamine | |
| CN112341413A (en) | Intermediate for synthesizing brivaracetam and preparation method thereof | |
| CN112341406B (en) | Synthesis method of trans-4- [4- (3-methoxy-4-nitrophenyl) -1-piperazinyl ] adamantane-1-ol | |
| CN115286504B (en) | Method for synthesizing (R) -2- (2- (tert-butoxy) -2-oxyethyl) pentanoic acid | |
| CN102757320B (en) | Method for preparing aliskiren intermediate | |
| CN114195684B (en) | Synthesis method of amino protecting group N-substituted chiral amino acid | |
| CN115340510B (en) | Preparation method of brivaracetam intermediate | |
| KR100340760B1 (en) | Stereoselective process for preparing (R)-(-)-muscone | |
| CN118684567A (en) | Method for synthesizing (2S) -2-benzyloxy-3-pentanone | |
| CN100469759C (en) | Toremifene crystallization method | |
| CN102757399B (en) | Preparation method of aliskiren intermediate | |
| CN105037318A (en) | 2-cyano-3-(2,2-difluoro-1,3-benzodioxyl-4-yl)acrylic compounds and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |